


Babysitting

by Sunglows



Category: Supernatural
Genre: Alternate Universe - Castiel, Alternate Universe - Dean winchester, Alternate Universe - John Winchester, Alternate Universe - Mary Winchester, Alternate Universe - Sam Winchester, Dean Winchester - Freeform, Dean Winchester as a dad, Dean Winchester is Sam Winchester's Parent, Dean Winchester owns a company, Dean is Bad at Feelings, Dean-Centric, Destiel - Freeform, F/M, Female POV, Female reader insert, Hardworking Dean Winchester, Hurt Dean Winchester, Jared Padalecki - Freeform, Jensen Ackles - Freeform, Mark of Cain, Megstiel - Freeform, Misha Collins - Freeform, POV Female Character, Protective Dean Winchester, Reader Insert, SPN - Freeform, SPN family, Sam Winchester - Freeform, Sam and Dean Winchester - Freeform, Spn fandom, Spn fans, Spn female reader insert, Supernatural - Freeform, Supernatural AU - Freeform, Supernatural Fandom - Freeform, Supernatural Reader insert, Supernatural fans - Freeform, Supernatural female reader insert, The Family Business, castiel - Freeform, crowley - Freeform, mark sheppard - Freeform, sam and dean - Freeform, spn reader insert, supernatural family
Language: English
Status: Completed
Published: 2017-08-31
Updated: 2017-08-31
Packaged: 2018-12-21 23:25:41
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,783
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/11954886
Author URL: https://archiveofourown.org/users/Sunglows/pseuds/Sunglows
Summary: Dean Smith is a busy working man who struggles to find someone to watch his three kids. Lucky for him, you put up flyers around your hometown offering to babysit. What happens when his kids grow older and no longer need a babysitter?





	Babysitting

You’ve decided to try babysitting for some extra cash and you were about to give up hope and stop sticking up your number around town to babysit. You made over one hundred bright pink flyers, each one with strips of your number on the bottom.

You had been hanging up flyers for the past month now, but who in their right minds would hire a stranger to babysit their kids?

You thought maybe babysitting was a good idea for the extra cash. You were currently attending school at some nearby college and still lived with your parents because let’s be honest, it’s hard to take classes, work and live by yourself. 

But living with your parents with no job meant that you were always broke. Want to go eat? Broke. Want to go shopping? Broke. Want to go somewhere nice? Broke.

You were tired of it. You wanted your own money to buy yourself your own things instead of having to ask your parents, and also to maybe help your parents with some overly-priced bills.

It was getting dark and you decided that hanging up seventy flyers was enough for the day and that you will just continue to hang the rest tomorrow. You got home and your dad was home from work, and your mom was cooking.

“Honey, dinner is almost ready!” Your mom shouted to you as you began walking upstairs to your room.

“No thank you, mom. I ate just before I left. I’m just going to head to my room.” You said back to her.

You continued to your room and threw your bag on the floor and flopped yourself onto your bed, another unsuccessful day.

Your bones cracked a few times as you laid yourself flat on your bed and you sighed. You’re not getting any younger and you wished you could flash forward to when you had a stable job and your own home.

You began to drift off into a slumber when your phone began to ring, making you jump quite hard.

You ran to your bag on the floor and quickly unzipped it, taking your phone out and answering the unknown number that was calling.

“Hello?” You grimaced at the sound of your disgusting scratchy voice, caused by your almost sleep a few seconds ago.

“Yes, hello. My name is Dean Smith and I’m calling about this babysitting service that you posted up on this flyer?”

The voice almost made you wet your pants. The man’s voice was so deep and sexy that you already wanted to see what this man looked like and who he was.

“Yes, that’s me! What can I help you with?” You asked with a voice that you tried to make it sound like you were purely business, but you were failing miserably.

“I was wondering if maybe you can come to my house tomorrow so I can ask you some questions about yourself? I want you as a babysitter for my kids but I just want to get to know you before allowing you to watch them. Will that be okay? At around three in the afternoon?”

“Sure thing!” You replied a little too embarrassingly loud.

“Okay then, it’s settled. Do you text? If you do, I’ll just send you my house address.”

“Yes I text.” Was all that you said, and you felt like you should’ve said more.

“Okay then! I’ll just text you. Good-bye!”

You said bye back and you both hung up. You waited impatiently for the man to send you his address. When he did, you quickly put the address into Google maps.

“Holy cow!” You couldn’t believe where this man lived. He lives in the Beverly-Freaking-Hills! What the hell would this man want with a person who needs to put out flyers to find a job rather than finding some professional?

Honestly, you were now intimidated. This man, his wife and his kids probably have it all.

You put your phone on your charger and got back into bed. You closed your eyes to fall back asleep and your dreams were filled with nothing but that voice on the other side of the phone and guesses on what the man looked like.

::

You hadn’t done anything all day because you were nervous to meet this man.

“This man lives in Beverly Hills, mom!”

“Well maybe he just wants to help someone out. Plus, maybe he will make you his girlfriend in the long run.” Your mom winked your way, making you blush at her words.

“Doubt it. He has kids, so that must mean he has a wife, right?” You asked your mom as you picked at your salad.

“Not necessarily. The mom might not be in their lives.”

You thought your mom was right. If two adults, one man and one woman, needed a babysitter, you would think the woman would call. But you guessed you would find out soon enough.

It was time to leave so you got into your small 1967 red Chevrolet Malibu, and you made your way up town.

Half an hour later, you made your way into a huge community filled with homes that you never seen so big. You were amazed by the way these homes looked. They all had to be at least three stories high.

Your driving came to a slow halt as you found the house with your GPS. You parked your car on the street, right outside the big white home, and walked up to the door.

You nervously rang the doorbell and waited impatiently.

A man no later than his late thirties, in a nice white shirt, opened the door and smiled widely at you. “Hello, come in.”

You walked in and the house smelled like cleaning product, as the house looked completely spick and span. Not a single dirt spot anywhere. 

The man lead you to an office room that was on the second story of the house, and gestured you to sit at a table right next to him. He looked up at you and the sun shining in from the window within the room, made you fall in love with his eyes. His eyes were rainforest green and you couldn’t believe how green they were. Yet, here you were with boring Y/E/C eyes that more than half the world has.

“So to start off, can I get a name?” The man asked you. You began to speak and his cologne lingered into your nostrils, making him sexier now that he smells good too.

“My name is Y/N.”

“Okay, Y/N, tell me about yourself.” The man stared at you and your heart began to beat against your ribcage and you felt like the man could hear your heart beats.

“Well I’m twenty-four years old. I’m currently attending a college within my hometown with a major in English. I am the second child out of four within my immediate family. I love children. I’ve volunteered numerous times at elementary schools and at summer camps.”

The man smiled, satisfied with your answer. “Do you have any children of your own? A family of your own?”

You were quite embarrassed at his question. Should you have had a family by now? Did he have a family by the age of twenty-four?

“Uh, no, I don’t.” You responded.

“Any boyfriends or husbands that I should know about?” He asked, looking straight into your eyes.

“No, sir.” You replied simply.

He continued to smile and it began to make your hands sweat.

“Please, call me Dean,” He started. “So it looks like I’m going to hire you. I was thinking maybe I could pay you $50 per hour?”

Your eyebrows raised in amazement. You were only going to ask for $50 per day.

“You’re right, that’s not enough. How’s $75 per hour?”

You began to laugh because Dean clearly took your expression the wrong way. “That’s more than enough. What times would you need me to babysit?”

“Okay now don’t be mad, but I’m going to need you to babysit overnight. From seven in the evening to seven in the morning. I’ll be home by then and I’ll be able to get the kids up and ready for school, so don’t worry about that.”

Jesus Christ! Twelve hours! You thought if you would ever be able to sleep in your own bed again if you took this job.

Your hesitation to say yes to the job made Dean continue to talk. “I have several guest rooms in here, but unfortunately only one of them is fully equipped. It also has a restroom within the room, and that’s where you will be staying. The room is between my room and the kids room.”

Would it really be so bad to take the job? Maybe you can sleep at home on the weekends and on weekdays stay here. So that means, you would have to come to his house straight after school, considering you get out of school at six in the evening. Not to mention, that’s $900 for every time you babysit!

“I’ll take it.” You stated.

Once again, Dean smiled and it looked like his eyes became greener. He bent over to you and took you into his arms in a big hug, which surprised you only a lot.

You hugged back, patting his back and he continuously thanked you for taking the job.

He pulled away and got up. You got up as well and he stopped in the doorway. “Come meet my kids.”

You both walked down the stairs and into the living room where a huge t.v. screen played Spongebob.

“Kiddos, I want you to meet someone!” All the kids ran to their dad as you made a head count of how many children you would be watching. Three kids, not too bad.

“Sam, John and Mary, meet Y/N!” Dean said happily to the kids.

All three kids smiled at you and ran to you in a big hug. You made a slight oomph, as the children squeezed a little too hard.

“They’re so cute and loving. I see they’re huggers too. Get it from their dad?” You laughed.

Dean laughed too. “Sorry about that hug. Ever since their M-O-M left a few years ago, it’s been hard to take care of them and run a company.” He stated.

Your eyes widened as he mentioned his occupation. “You run a company? No offense, but why in the world would you want to hire someone who isn’t all that experienced whereas there’s professionals everywhere that would be more than willing to take your money?”

Dean hesitated to answer and you could tell he was thinking before he decided to answer you. “You’re right. But unfortunately, professionals keep everything strictly professional. I would much rather have a family person who needs the money and loves family just as much as me. Family means everything to me. I was once a struggling kid in college and I know you are as well, otherwise you wouldn’t have taken a job caring for three little maniacs.”

You and Dean both laughed as he called his kids maniacs.

“One more thing, let me show you around the house.”

Dean showed you the whole house and it was practically a work out. The kitchen was as big as your room and you couldn’t wait to cook in it. He had several living rooms, although in your opinion you thought that was useless. He had three bathrooms downstairs as well as three bedrooms. Up the stairs, he showed you the theater room which astounded you, and he showed you his office room as well as the master bedroom, the fully furnished guest room, the laundry room and the kids rooms. On the third story, there was a huge storage room as well as several other rooms that Dean said he was too lazy to show you.

You both walked back down both flights of stairs and he took you to his backyard patio. He showed you the huge pool and jacuzzi as well as the tiki bar and the giant game room that was to the left.

“So I was wondering if maybe you could start tomorrow? You are more than welcomed to eat whatever is in the fridge. I have a maid that comes over so she will be here when you get here. She usually makes dinner for the kids, cleans, does laundry, and then leaves.”

You nodded in understanding.

“Okay it’s settled then. You are welcomed to stay and get to know the kids or me, maybe.”

You looked up at Dean and he was blushing, but he stared into your eyes to make it seem like he was being totally normal.

“I actually have to get home and help my mom with dinner. But I just want to say, thank you so much Dean. For this opportunity. I was really hoping for someone to call me back. I’ve tried for a long time now and you’re the only person who needed a babysitter.”

“No problem, Y/N. I will walk you out.”

He walked you out as you stepped out of his home and he walked you to your car.

“Have a thing for classic cars, I see?” Dean gestured towards your car.

“Yes. They are my weakness.” You smiled at him as he practically drooled over your car.

“I actually have a black ‘67 Chevy Impala in my garage along with several other cars, but my Chevy is my baby. I need to show you them, but that’s due for another day.” He smiled.

You decided to walk up to him and hug him. He smelled so good and you felt his big muscled arms wrap around you and for a second, you thought he ran his fingers through your hair.

You got into your car after you thanked him practically a million times, and you drove back home, happier than ever that you found a place that would pay you good. Plus, the dad is hot and the kids are sweet.

::

Four years later and you finally saved up enough money and helped your parents pay enough of their bills, that you decided it was finally time to move out.

You got yourself a nice small apartment, not too far from your old home, that was surprisingly cheap. The environment around the apartment was peaceful and quiet and the little porch outside of your sliding door windows received enough sunlight for your daily reading. You finally graduated with your degree in English, feeling accomplished.

You still continued to babysit Dean’s children. Although, they were so much more older now. Mary is now twelve, John is eleven and Sam is ten. Crazy ages.

Now that Mary was getting older, she was developing a major attitude now especially towards Dean. But for some reason, not unknown to you, she always vented to you about the latest gossip in her middle school and who was holding hands with who.

John is such a game nerd, but he sure does have an infinite amount of knowledge when it comes to technology. You recently got a new phone and didn’t know how to work the camera, but John quickly became acquainted with your phone and helped you out. He even showed you how to use it step by step.

Sam on the other hand, he was such a quiet kid but super sweet at the same time. He loved to read books. What you decided to do was bring him a new book every two weeks, since he reads them that quickly anyways. The new books that you bring always light up his face like if it’s Christmas.

You grew to love these kids. You seen them everyday that they became family to you. It would be unusual if you didn’t babysit them that day, like if something was missing.

“You know, Sam, Mary and John are getting older now.” Dean said softly before he left to work.

You nodded your head in agreement as you watched the kids do their homework. You were chewing on a carrot stick that you originally pulled out for the kids to munch on.

“They’re getting old enough to watch themselves now.”

You finally knew where this was going. You stopped chewing and looked at Dean. He had a sad expression on his face.

“What are you saying, Dean?” You wanted him to be straightforward, but that was definitely something you learned that he was not well at doing over the course of four years.

“I’m sorry Y/N. But unfortunately, these kids are getting older and I won’t have a need for a babysitter anymore. Mary is going to be thirteen in a few months and she is mature enough to be alone and take care of her brothers.”

He was whispering now, and you knew he didn’t want the kids to hear. You knew they would be heartbroken if they knew you weren’t going to babysit anymore.

“You’re firing me?” You began. Tears started to flow and your throat was burning from trying so hard to hold back tears. “Dean please. I love your kids. Don’t do this please. They are my family. You are my family.”

Dean looked doleful, but you knew he meant what he said and he wasn’t going back.

“Today will be the last day. I have to go to work now.”

And then he left. Just like that. Clearly he didn’t realize the attachment you had with his kids. Or maybe he just didn’t care?

You didn’t know what you were going to do and you were becoming scared. Of course you still had your parents and your brother and sisters but unfortunately for you, your brother and sisters lived in other states and you know your parents love being alone now that you’ve moved out.

Once Dean left, the time seemed to pass by quick. Mary spoke to you about school and you hugged her a little longer after her discussion about school. You played games with John a little longer than usual, knowing that it will be the last time. You talked books with Sam, expecting to miss what a smart kid he was about everything because of the many books he’s read.

Night came by and the morning came quicker. Dean walked into the guest room to wake you of your slumber.

“You can go home now. I left your last paycheck on the counter.” He whispered.

You looked at his face, but he was blank. Nothing showed across his face and it made you feel worse. You remembered last night. You cried yourself to sleep knowing you won’t see these kids anymore. Or Dean.

You knew you were going to miss Dean a lot as well. He was so kind and generous to you. He’s even taken you out on a few dates as well when he didn’t have work and when the kids were at school. You thought being fired was your fault, but you couldn’t remember doing anything wrong.

You left the Smith residence quickly, not wanting Dean to see any tears fall from your face as you exited the house. You got into your red Chevy and drove home.

It was quiet. But now, it was too quiet for your liking and you didn’t like to be alone with your thoughts. You kept thinking maybe you said something to the kids and they repeated what you said to Dean. Or maybe it was that time that you forgot to throw away the trash that the kids left on the counter. Or maybe it was that time you let the kids go in the pool when it was cold, but they kept begging.

You realized now, that you had to go out and get a real job. Thank goodness for your education.

Quicker than you could register, you found a decent paying job being an editor at some magazine company in Los Angeles. Of course it was quite a travel from your home, but your hometown was the country and not the city.

You weren’t feeling the hype of being an editor. You made some friends outside of work and they always became thrilled when you told them that you were an editor at Los Angeles Magazine. Literally all you did was edit people’s journal entries for the magazine, and that was it.

You missed babysitting. You tried getting them and Dean off of your mind, but everything you did reminded you of them.

Whenever your friends gossip, guess who it reminded you of? When you passed by the many billboards of new video games, guess who it reminded you of? Guess who it reminded you of when you tried to read on your porch?

Worst of all, guess who you remembered working at a company owned by one of the most wealthiest men in L.A.?

You hated it but you were helpless. You couldn’t do anything. You tried calling Dean to at least talk to the kids, but he changed his number which made your heart break. Before he changed his number, he even told you not to come back to his house.

Months passed by and you were still unhappy with your job and everything that surrounded you. Your mom insisted you move back in with them if you hated your job so much. But you couldn’t do that to them. They struggled trying to feed three people, you didn’t want to put them through that again.

Your routine was always the same. Wake up, go to work for an eight hour shift, have dinner with yourself, and then go home and clean up your house or maybe do some laundry. It was lonely and you didn’t feel this way before. The quiet turned into an annoying silence that was driving you insane.

Today was the same thing again. You separated your clothes and put them into the washer and then walked back to your apartment. The bad thing about the complexes were that you had to share a washer and a dryer.

You walked back to your apartment with your hamper in your hand when you seen a man squatting down with his head in his hands, right in front of your door.

The man was wearing grey sweats and a blue pullover sweater, but you knew he wasn’t homeless because he was wearing clean Nike shoes and his clothes were clean.

“Um, sir? Do you need something?”

You heard the man sobbing as you walked closer to him, but stopped when you spoke. He looked up and those eyes were the same ones that drew you in the first time you met him.

“Dean? What are you doing here?” You became frantic when you assumed something was wrong if Dean was at your front door, crying.

Dean got up from his position and walked to you and pulled you into a hug. The calming smell of him suddenly pulled you back into your memories and you began to hug him back. You rubbed his back until he pulled away first.

“I’m so sorry.” Was all he said as he was shaking from crying so much.

“It’s okay, Dean. Tell me, what happened?”

“I need you back. The kids need you back. We all miss you so much. I’m so sorry I fired you. I never should have told you to leave.”

You brought your hand up and wiped the tears from Dean’s soft face, your other hand going to his shoulder.

“Dean it’s oka…”

“It’s not okay! Okay? I fired you because I’m a sissy that couldn’t tell you my real feelings for you. So I pushed you away thinking it would make things better but I only thought of you even more!”

You were completely startled by his sudden rush of honesty of his feelings for you. Your hands dropped to your sides as you tried to process what Dean just said.

He has feelings for you. Do you feel the same? Of course you do, otherwise you wouldn’t have felt so depressed from the time he fired you.

“Dean, I…”

“Please, if you don’t feel the same way, just say it. Don’t hold back.”

“Dean, I love you Dean. I love your kids too. So much. I’ve loved you for a long time but I never thought you would want to be with me because I thought you were always just too busy to be with someone. But then, if you have feelings for me, why did you fire me?”

Dean turned his back towards you as you waited patiently for his answer. A few seconds passed and he turned back around to answer you.

“At first it was just a friendly relationship that we had. I loved how happy you made my kids and that made me happy. A year passed by and I noticed I was becoming attached to you. That’s when I started inviting you over even on your days off. Two years passed and I realized my feelings for you were way more than just liking. I was starting to love you and it was scaring me. So I began to work later shifts. I would come home later than usual and I made the kids go to school later. Finally, I just couldn’t handle it. You were constantly on my mind, so that’s why I did what I did.”

Dean was fidgeting and swaying side to side nervously, but continued to talk.

“At first I told the kids you found a new job and you were too busy to babysit them. I got a new babysitter but it just wasn’t the same. At night, I would hear the kids go to bed crying. There wasn’t a day I didn’t think of you, Y/N.”

You were so mesmerized by what he said that you grabbed him by his big shoulders and smashed his lips to yours. You had to do it. The urge was becoming too strong and you had a feeling he wasn’t going to make the first move any time soon.

Your arms wrapped around his neck and his arms wrapped around your waist as your lips and his lips molded and became one. His lips were soft and felt exactly the way you imagined it would and you had the feeling in your stomach that you imagined you would get if you ever kissed him.

But this was it. You were kissing him and holding him and you didn’t want to let go. You’ve never loved a man as much as you loved Dean Smith.

::

“Mom, can I go out with some friends tonight?” Mary asked you.

“Of course sweetheart. Just don’t be out too late. Call me if anything happens and you know I’ll be there.”

“Mom, can we go to the library?” Sam asked coming out of his room.

You nodded and smiled as he smiled widely and excitedly.

“Mom, I want this game. Can you get it for me when you have money?” John asked so nicely.

“Sure. As long as it’s not a violent game, I’ll be more than happy to.” You replied.

“Hey sweetheart.” Dean came up to you and kissed you on your temple as you were making dinner. Dean finally cut his own hours to spend more time with his family. You and him. Yours and Dean’s yearly income was way over the top and you two didn’t have to work so much. You also didn’t have to travel as far, so you kept your job in Los Angeles now that you lived in the rich community of Beverly Hills.

“You know I love you right? And the kids love you?” Dean said as he massaged my shoulders.

“Of course Dean. I love you guys too. So much.” You continued to cut vegetables to make some soup that your mom was more than happy to share the recipe with you.

You dunked the vegetables in the pot and turned towards Dean. He wrapped his arms around your waist and you wrapped your arms around his neck. Dean looked down and smiled, caressing your stomach. He lowered himself and placed a soft kiss on your tummy.

“I especially love our upcoming special addition to our family.”

You pecked Dean on the lips as he got back up and you pulled away from him. He wrapped his arms around you from behind and began to rub your eight month big tummy.

“Yes. I especially love our little Cassie that will soon be joining us.”

You smiled as you felt little Cassie kick and you knew at that moment that you have never felt happier.


End file.
